[(3,5-dimethoxy-phenoxy)methyl]oxirane | 41279-92-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(3,5-dimethoxy-phenoxy)methyl]oxirane
• 英文别名: 2-((3,5-dimethoxyphenoxy)methyl)oxirane；2-[(3,5-Dimethoxyphenoxy)methyl]oxirane
• CAS: 41279-92-9
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: YQDLFJHWIXBSCI-UHFFFAOYSA-N

物化性质

• 熔点：
  61.5-63.4 °C
• 沸点：
  336.7±22.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(3,5-dimethoxy-phenoxy)methyl]oxirane 在 gold(III) chloride 、 silver trifluoromethanesulfonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 5,7-dimethoxychroman-3-yl 3-methoxybenzoate
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationships of EGCG Analogues, a Recently Identified Hsp90 Inhibitor

  摘要：

  Epigallocatechin-3-gallate (EGCG), the principal polyphenol isolated from green tea, was recently shown to inhibit Hsp90; however, structure activity relationships for this natural product have not yet been produced. Herein, we report the synthesis and biological evaluation of EGCG analogues to establish structure activity relationships between EGCG and Hsp90. All four rings as well as the linker connecting the C- and the D-rings were systematically investigated, which led to the discovery of compounds that inhibit Hs90 and display improvement in efficacy over EGCG. Antiproliferative activity of all the analogues was determined against MCF-7 and SKBr3 cell lines and Hsp90 inhibitory activity of the four most potent analogues was further evaluated by Western blot analyses and degradation of Hsp90-dependent client proteins. The prenyl-substituted aryl ester of 3,5-dihydroxychroman-3-ol ring system was identified as a novel scaffold that exhibits Hsp90 inhibitory activity.

  DOI：

  10.1021/jo401027r
• 作为产物：
  描述：

  3,5-二甲氧基苯酚 、 环氧氯丙烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以79%的产率得到[(3,5-dimethoxy-phenoxy)methyl]oxirane
  参考文献：
  名称：

  pterocarpenes和coumestans的合成通过区域选择性环脱水†

  摘要：

  描述了一种高效的合成方法，可合成萜烯和香豆素。在温和的条件下，BCl 3介导的1,3-二芳氧基丙酮的脱水环化使区域选择性闭环，得到3-（（2-碘芳氧基）甲基）苯并呋喃，其通过Pd催化的分子内直接芳基化反应转化为相应的茂木。随后的苄基氧化导致香豆素。该序列被应用于香豆酚的形式合成和拟合成的木瓜素结构，以及氟苯丙胺类化合物B和C的总合成。

  DOI：

  10.1039/c6ob01451h

文献信息

• An Au-Catalyzed Cyclialkylation of Electron-Rich Arenes with Epoxides To Prepare 3-Chromanols
  作者：Zhangjie Shi、Chuan He

  DOI：10.1021/ja031953a

  日期：2004.5.1

  A gold-catalyzed cyclialkylation of electron-rich arenes with tethered epoxides afforded 3-chromanols stereospecifically.

  金催化的富电子芳烃与环氧化物的环烷基化反应得到立体特异性的 3-苯并二氢呋喃。
• .beta.-Adrenergic blocking agents. V. 1-Amino-3-(substituted phenoxy)-2-propanols
  作者：Albert F. Crowther、D. J. Gilman、B. J. McLoughlin、Leslie Harold Smith、R. W. Turner、T. M. Wood

  DOI：10.1021/jm00304a018

  日期：1969.7
• Synthesis and Structure–Activity Relationships of EGCG Analogues, a Recently Identified Hsp90 Inhibitor
  作者：Anuj Khandelwal、Jessica A. Hall、Brian S. J. Blagg

  DOI：10.1021/jo401027r

  日期：2013.8.16

  Epigallocatechin-3-gallate (EGCG), the principal polyphenol isolated from green tea, was recently shown to inhibit Hsp90; however, structure activity relationships for this natural product have not yet been produced. Herein, we report the synthesis and biological evaluation of EGCG analogues to establish structure activity relationships between EGCG and Hsp90. All four rings as well as the linker connecting the C- and the D-rings were systematically investigated, which led to the discovery of compounds that inhibit Hs90 and display improvement in efficacy over EGCG. Antiproliferative activity of all the analogues was determined against MCF-7 and SKBr3 cell lines and Hsp90 inhibitory activity of the four most potent analogues was further evaluated by Western blot analyses and degradation of Hsp90-dependent client proteins. The prenyl-substituted aryl ester of 3,5-dihydroxychroman-3-ol ring system was identified as a novel scaffold that exhibits Hsp90 inhibitory activity.
• Syntheses of pterocarpenes and coumestans via regioselective cyclodehydration
  作者：Maloy Nayak、Youngeun Jung、Ikyon Kim

  DOI：10.1039/c6ob01451h

  日期：——

  pterocarpenes and coumestans is described. BCl3-mediated dehydrative cyclization of 1,3-diaryloxyacetones under mild conditions permitted regioselective ring closure to afford 3-((2-iodoaryloxy)methyl)benzofurans which were converted to the corresponding pterocarpenes by Pd-catalyzed intramolecular direct arylation. The subsequent benzylic oxidation led to coumestans. This sequence was applied to the formal

  描述了一种高效的合成方法，可合成萜烯和香豆素。在温和的条件下，BCl 3介导的1,3-二芳氧基丙酮的脱水环化使区域选择性闭环，得到3-（（2-碘芳氧基）甲基）苯并呋喃，其通过Pd催化的分子内直接芳基化反应转化为相应的茂木。随后的苄基氧化导致香豆素。该序列被应用于香豆酚的形式合成和拟合成的木瓜素结构，以及氟苯丙胺类化合物B和C的总合成。